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Chemical Compound Review

dodecoate     dodecanoate

Synonyms: laurate, vulvate, dodecanate, dodecylate, Dodecanoate, ...
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Disease relevance of lauric acid


High impact information on lauric acid

  • We report here a novel modification at the N terminus of the alpha-subunit of the photoreceptor G protein transducin, T alpha, with heterogeneous fatty acids composed of laurate (C12:0), unsaturated C14:2 and C14:1 fatty acids, and a small amount (approximately 5%) of myristate [5].
  • The laurate hydroxylase activities of cytochrome P450 2C2 or the catalytic domain with GFP fused to the C terminus were similar to the native enzyme [6].
  • Fatty acid exchange between albumin and model membranes (phosphatidylcholine bilayers) occurred on a time scale comparable to that for exchange among albumin binding sites, following the order octanoate greater than decanoate greater than laurate [7].
  • When examined by mass spectrometry, about two-thirds of the lipid A molecules isolated from wild type E. coli grown at 12 degrees C contained palmitoleate in place of laurate, whereas the lipid A of cold-adapted MKV11 contained only laurate in amounts comparable with those seen in wild type cells grown at 30 degrees C or above [8].
  • We show that undecanesulfonate and laurate are mutually competitive inhibitors, supporting the hypothesis that fatty acid anion is transported by UCP1 [9].

Chemical compound and disease context of lauric acid


Biological context of lauric acid


Anatomical context of lauric acid

  • An adult rat heart myocyte preparation was used to study the uptake and metabolism of the 1-(14)C-labeled free fatty acids decanoate, laurate, myristate, palmitate, and oleate at 37 degrees C in the absence of serum albumin [18].
  • The formation of the latter is correlated accurately to laurate hydroxylase activity studied concurrently in microsomes prepared from the liver of these animals [19].
  • There was no significant change in the enzyme activities of laurate hydroxylase (cytochrome P450IVA1) or acyl-CoA oxidase in the first 8 h after treatment, but the activities had doubled at 24 h, suggesting that these enzymes are not involved in the mediation of early events in peroxisome proliferation [20].
  • The mutant C2A2, in which two alanines were substituted for the linker, had no detectable laurate hydroxylase activity in COS-1 cells, and minor amounts of hemoprotein for this mutant were expressed in E. coli and insect cells [21].
  • Induction of peroxisomal fatty acyl-CoA oxidase and microsomal laurate hydroxylase activities by beclobric acid and two metabolites in primary cultures of rat hepatocytes [22].

Associations of lauric acid with other chemical compounds


Gene context of lauric acid

  • Furthermore, a strong correlation (r = 0.89; P < 0.001) was found between immunochemically determined CYP4A11 content and laurate omega-hydroxylase activity in liver samples from 11 different subjects [28].
  • While the P450 responsible for microsomal laurate omega-1 hydroxylation in human liver has been identified as CYP2E1, the enzyme catalyzing omega-hydroxylation remains poorly defined [28].
  • Function of the Escherichia coli msbB gene, a multicopy suppressor of htrB knockouts, in the acylation of lipid A. Acylation by MsbB follows laurate incorporation by HtrB [29].
  • The long-chain fatty acids stearate (18:0), arachidate (20:0), and lignocerate (24:0) reproduced palmitate's effects on these events, while saturated fatty acids with shorter hydrocarbon chains [i.e., laurate (12:0) and myristate (14:0)] failed to induce ceramide accumulation or inhibit Akt/PKB activation [30].
  • In contrast to htrB, extracts of strains with insertion mutations in msbB are not defective in transferring laurate from lauroyl acyl carrier protein to (Kdo)2-lipid IVA [29].

Analytical, diagnostic and therapeutic context of lauric acid

  • Threonine-301 from rabbit liver cytochromes P-450 (laurate (omega-1)-hydroxylase and testosterone 16 alpha-hydroxylase) has been replaced by histidine via site-directed mutagenesis [31].
  • We have analyzed the isotopomer abundance ratios of an equimolar mixture of nine fatty acid methyl esters (decanoate, undecanoate, laurate, tridecanoate, myristate, pentadecanoate, palmitate, heptadecanoate, and stearate) by selected-ion monitoring gas chromatography/electron impact/mass spectrometry (GC/EI/MS) [32].
  • In this study, four steers were administered [3H2]- and [2H3] 17 beta-19NT laurate (2 mg kg-1 body mass) by intramuscular injection and blood, urine, faeces and bile samples were taken for 30 d until slaughter, after which tissues were sampled for total residue analysis [33].
  • Lipase-catalyzed reactions, hydrolysis of triprionin and nitrophenyl laurate, were selected to test the system and demonstrate the feasibility of immobilization of enzymes to the membranes of liquid-core capsules and the ability to extract hydrophobic products of the reaction within the capsule core [34].
  • The walking capacity of the animals (treadmill test) was evaluated at different times and up to 5 weeks after Na laurate injection [35].


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